Here’s How to Spend a Relaxing Weekend in Rhinebeck

The historic Hudson Valley town packs boutique shopping, gourmet eats, and cultural to-dos in just a few square blocks.

Wikimedia Commons | Photo by Daniel Case

The historic Hudson Valley town packs boutique shopping, gourmet eats, and cultural to-dos in just a few square blocks in Dutchess County.

Long before cities like Beacon and Hudson lured New York City weekenders and out-of-towners, Rhinebeck served as the go-to Hudson Valley retreat. These days, the Dutchess County spot is as charming as ever, with its abundance of boutique shops, manicured sidewalks, and on-trend restaurants.

Regardless of whether you visit on the regular or have never stepped foot into town before, make this the year you take advantage of all that Rhinebeck has to offer. Try our guide first, then make your own when you plan a return trip — which you will.

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9:30 a.m. – Start the day on a sweet note at Samuel’s

Every day, without fail, locals and visitors alike flock to Samuel’s Sweet Shop for coffee, candy, and confections. The spot serves Partners coffee to balance out the sugar-centric menu. Pair your caffeine with a fresh apple turnover, muffin, or any other pastry on offer that morning. If you happen to pick up a bit of candy while you’re there, we don’t blame you.

42 E Market St, Rhinebeck


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10:30 a.m. – Explore Wilderstein Historic Site

Located in the heart of the Hudson Valley, Wilderstein Historic Site charms with its Queen Anne-style design and expansive grounds. On select dates throughout the year, visitors can tour the mansion and explore the vintage treasures that the Suckley family amassed during their three generations inside the house. Outside, 40 acres of manicured gardens and grasses call to hikers and walkers.

330 Morton Rd, Rhinebeck

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12 p.m. – Eat farm-to-table with a twist at The Amsterdam

The Amsterdam brings European flavor to Hudson Valley cuisine in the heart of Rhinebeck. Open for brunch, lunch, and dinner, on select days during the week, The Amsterdam delights with tapas-style bites like a burrata, avocado tartine, and own house-made ricotta. After a meal, stop by the fine food and provisions market for onsite shopping to give your pantry an artisanal upgrade.

6380 Mill St, Rhinebeck

1:30 p.m. – Fly high at the Old Rhinebeck Aerodrome

If you visit Rhinebeck over the weekend, don’t leave without making a trip to the Aerodrome on a Saturday or Sunday afternoon. That’s when the airshows, the high-flying spectacles with historic planes and skilled pilots, take place. Biplane rides are available both before and after the shows, and the museum is open daily.

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9 Norton Rd, Rhinebeck


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4 p.m. – Shop and stroll along Market and Mill

When it comes to shopping, Rhinebeck is a dream destination. With quaint boutiques lining the picturesque Market and Mill Streets, it is all too easy to lose track of time as you hop from one storefront to the next.  For a truly unique experience, head to A.L. Stickle, Megabrain Comics, or Oblong Books & Music. They’re the perfect places to find a one-of-a-kind gift or the knickknack you never knew you needed.

6:30 p.m. – Dine in style at Terrapin

As the winner of not one, but three awards in our 2020 Best of Hudson Valley Awards, Terrapin is a required stop on any successful trip to Rhinebeck. For a more casual meal, head to the Red Bistro, where you can munch on Hudson Valley Cattle Company hamburgers, barbecue duck quesadillas, and artichoke and ricotta ravioli. On fancier occasions, make a reservation for the Dining Room, where you can savor the likes of Hudson Valley cheese plates, blue cheese-crusted filet mignon, and seasonal fruit crisp.

6426 Montgomery Rd, Rhinebeck

8 p.m. – Get a drink, and a history lesson, at The Tavern at The Beekman Arms

Instead of letting its historical origins fall to the wayside, the historic inn embraces them wholeheartedly. The 1766 Dutchess County building charms with an Americana aesthetic that includes an open hearth fireplace and a picturesque bar. Take it all in over a cheeky cocktail or Hudson Valley beer. Of course, the food is divine, too, in case you’re still feeling like a snack after dinner ends.

6387 Mill St, Rhinebeck

9 p.m. – Call it a night at Mirbeau Inn & Spa Rhinebeck

Mirbeau may be new-ish to the region, but it’s already a true Hudson Valley gem. The spa and hotel are both open for socially distant treatments and overnights, with full COVID-19 cleaning protocols in place. As for the rooms, they’re the ultimate in local luxury, thanks to thoughtful touches like cozy fireplaces, oversized bathrooms, and some of the most luscious beds we’ve ever seen.

46 W Market St., Rhinebeck

Related: The Best Way to Explore Millbrook

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The Big Sip, the Hudson Valley's premier wine and spirits fest, is October 7-8!